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Montemassi Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montemassi vacation rentals

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

1. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
$84 nightly
The price is $94
Oct 9 - Oct 10
Total with taxes and fees
Country House il Ciliegio
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

2. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."
Italy
Ivano
$80 nightly
The price is $90
Oct 23 - Oct 24
Total with taxes and fees
Agriturismo Benvenuti
A couple seated at a table with drinks, overlooking a pool area with lounge chairs and umbrellas.

3. Fattoria Maremmana

Fattoria Maremmana
4.0 star property
Grosseto
8.0 out of 10, Very good, (11 reviews)
"Staff very friendly and helpful. Very quiet stay as we visited at the beginning of the slow season. "
United States
James
$216 nightly
The price is $242
Oct 9 - Oct 10
Total with taxes and fees
Fattoria Maremmana
A person relaxing in a hot tub with a glass of wine.

4. Botrona B&B

Botrona B&B
Scarlino
9.4 out of 10, Exceptional, (26 reviews)
"Amazing B&B! Beautiful, clean, and very classy! Staff is excellent and friendly… breakfast is superb and staff’s hospitality is heart warming. Our stay was very pleasant. Home away from home… surprisingly beautiful grounds with jacuzzi and a sauna available whenever you want! Thank you!"
United States
Anna
$86 nightly
The price is $94
Oct 12 - Oct 13
Total with taxes and fees
Botrona B&B
A covered outdoor seating area with wicker furniture, a table, and potted plants.

5. Fattoria San Lorenzo - Apartments

Fattoria San Lorenzo - Apartments
Grosseto
8.8 out of 10, Excellent, (30 reviews)
"Great, clean, and beautiful place."
United States
Aimee
$75 nightly
The price is $86
Oct 14 - Oct 15
Total with taxes and fees
Fattoria San Lorenzo - Apartments
A building with a balcony with green shutters, potted plants, and a sign with the name "DOMUS SOCIALES".

6. Domus Socolatae Residenza d'Epoca Charming B&B

Domus Socolatae Residenza d'Epoca Charming B&B
Follonica
9.4 out of 10, Exceptional, (26 reviews)
"Our stay was amazing, will be back soon!"
United States
Tiffany
$108 nightly
The price is $118
Nov 2 - Nov 3
Total with taxes and fees
Domus Socolatae Residenza d'Epoca Charming B&B
A spacious living area with a dining table, red chairs, and a small round table. Large windows provide natural light and views of greenery outside.

7. Residence Il Boschetto

Residence Il Boschetto
Grosseto
8.6 out of 10, Excellent, (8 reviews)
"The house is gorgeous! The area is very nice and the amenities were great! "
United States
Enrique
$77 nightly
The price is $88
Oct 10 - Oct 11
Total with taxes and fees
Residence Il Boschetto
A stone fountain with a light-up base, surrounded by grass and trees, with a building in the background.

8. Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (34 reviews)
"We are very happy with everything in this hotel, nice room, comfortable bed, and very good breakfast."
Sweden
Tor
$77 nightly
The price is $89
Oct 21 - Oct 22
Total with taxes and fees
Fattoria Pian di Rocca
A modern living room with a sofa, a TV, a small potted plant, and a view of the outdoors.

9. Luci sul Mare

Luci sul Mare
Follonica
9.6 out of 10, Exceptional, (4 reviews)
"This place was so nice, clean and quiet. Just what I was looking for. It has been updated with all the latest things and even has a coffee maker and kettle for your use at any time during your stay in a shared hallway. I had a little balcony that I got to watch the sunset every nice which was lovely. Even better was the host as she helped me with some of my needs that I asked her for. I feel she went way above what she had to for me. I would stay here again if I were to visit Follonica again. "
United States
Tamara
$72 nightly
The price is $83
Oct 14 - Oct 15
Total with taxes and fees
Luci sul Mare
A beach with a thatched umbrella and two pillows on the sand.

10. Camping Maremma Sans Souci

Camping Maremma Sans Souci
3.0 star property
Castiglione della Pescaia
8.0 out of 10, Very good, (31 reviews)
"Very quiet cabin the woods - near to the beach. All in all works very well."
Italy
Paul
$32 nightly
The price is $38
Oct 10 - Oct 11
Total with taxes and fees
Camping Maremma Sans Souci
A modern kitchen with a built-in oven, stainless steel appliances, and decorative items on the shelves.

11. Il Bennu

Il Bennu
Gavorrano
$175 nightly
The price is $192
Nov 1 - Nov 2
Total with taxes and fees
Il Bennu
A modern hotel room with a large bed, a bedside table with a lamp, a small round table, a bench with towels, a large window with curtains, and a sign on the wall that reads "BEACH".

12. Marconi 1935 B&B and Holiday Home

Marconi 1935 B&B and Holiday Home
Follonica
9.4 out of 10, Exceptional, (10 reviews)
"Brilliant little apartment, lovely roof terrace with whirlpool. Easy walk to station and beach. Check in all done via WhatsApp and seamless, beds comfy bathroom.excellent. highly reccomend"
United Kingdom
Mark
$103 nightly
The price is $116
Oct 14 - Oct 15
Total with taxes and fees
Marconi 1935 B&B and Holiday Home
A beach with clear turquoise water, sandy shore, and a forested hill in the background.

13. Nautilus B&B Suite Design

Nautilus B&B Suite Design
Follonica
10.0 out of 10, Exceptional, (7 reviews)
"Was one of the better places I stayed on this trip loved the lights in the shower view was nice the rain head and the waterfall head need to be cleaned some water was coming out but they where pretty stopped up other then that excellent place to stay"
United States
James
$139 nightly
The price is $156
Oct 31 - Nov 1
Total with taxes and fees
Nautilus B&B Suite Design
A building with a tiled roof, a paved walkway, and potted plants.

14. La Residenza del Golfo

La Residenza del Golfo
Scarlino
9.0 out of 10, Wonderful, (19 reviews)
"Nice place. Simple and clean. Beach is 2 mins from the apartments. It’s a dog beach and is nice. Not the best in the area but certainly good enough for a quick escape to the beach. We were there for 2 weeks at the end of July and the beaches weren’t packed. The place is well air conditioned and clean. There are communal bbqs that are well maintained. Most people have dogs which is fine with us but might not be for everyone. Overall a simple, basic but pleasant stay and decent value. It’s near...
United Kingdom
Ashley
$173 nightly
The price is $190
Oct 9 - Oct 10
Total with taxes and fees
La Residenza del Golfo
A poolside dining table with a variety of pastries, fruits, and beverages, overlooking a swimming pool and a building with a tiled roof.

15. Residence la Pace - Pool & Relax

Residence la Pace - Pool & Relax
Grosseto
10.0 out of 10, Exceptional, (3 reviews)
"La struttura è molto bella, curata nei minimi dettagli e dotata di appartamenti nuovi. Il giardino e la piscina completano il quadro. La posizione è molto comoda, a circa 500 mt da Marina di Grosseto. Un ringraziamento alla famiglia che gestisce la struttura che ci ha accolto nel migliore dei modi e un grazie in particolare per la sopportazione delle nostre figlie che intrattenevano perennemente i gatti. Consigliatissima e adattissima per un viaggio in famiglia. Grazie"
Italy
simone
$104 nightly
The price is $115
Oct 18 - Oct 19
Total with taxes and fees
Residence la Pace - Pool & Relax
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

16. Nido con vista

Nido con vista
Radicondoli
$134 nightly
The price is $148
Nov 7 - Nov 8
Total with taxes and fees
Nido con vista
A small outdoor area with steps leading to a door, surrounded by potted plants and a tree.

17. Residence I Mari

Residence I Mari
Castiglione della Pescaia
$185 nightly
The price is $207
Oct 14 - Oct 15
Total with taxes and fees
Residence I Mari
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montemassi Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Nice and quiet excellent hospitality"
Mohammed 2-night trip
Posted 2 days ago
Castiglion del Bosco, A Rosewood Hotel

Find out more about Montemassi

Everything you need to know about Montemassi vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montemassi vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montemassi vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montemassi vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montemassi. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montemassi in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $38 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montemassi rentals

At Expedia, we put the best Montemassi vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montemassi rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montemassi vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montemassi. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Montemassi?

Yes, we give you a choice of vacation rentals near popular local attractions in Montemassi, or you can select a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Montemassi?

Casa Viale Italia - homely house with direct access to the sandy beach: Visitors like this Montemassi vacation home rental. It is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Montemassi?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Montemassi stay.

What’s there to see and do in Montemassi?

While exploring the area, visit family-friendly sights like Piscina Il Giunco, or get outside and enjoy nature at Lago dell'Accesa. Podere Ristella Vineyards and Winery and Rocca di Frassinello Winery are a couple of places you'll find in the larger area.

What’s a vacation rental in Montemassi like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Montemassi. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.